# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1553780'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-08-24 downloaded from the CCDC.
;
_audit_creation_date             2016-12-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H17 N O2'
_chemical_formula_weight         279.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.3952(13)
_cell_length_b                   9.4580(19)
_cell_length_c                   12.085(2)
_cell_angle_alpha                102.98(3)
_cell_angle_beta                 94.15(3)
_cell_angle_gamma                90.64(3)
_cell_volume                     710.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2325
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4804
_cell_measurement_theta_min      3.6698
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.332
_exptl_crystal_size_min          0.197
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9148
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.73
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 98.6000
_diffrn_measured_fraction_theta_max 27.4804
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9056
	          2theta: -19.8803
scan:
	Number of images: 338
	           Slice: -110.0000 - 59.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 44.9056
	          2theta: -19.8803
scan:
	Number of images: 334
	           Slice: -110.0000 - 57.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9056
	          2theta: -19.8803
scan:
	Number of images: 182
	           Slice: -65.0000 - 26.0000
	     Image width: 0.5000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.9056
	          2theta: -19.8803
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             3206
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0629
_diffrn_orient_matrix_UB_12      -0.0508
_diffrn_orient_matrix_UB_13      0.1344
_diffrn_orient_matrix_UB_21      -0.0261
_diffrn_orient_matrix_UB_22      -0.0954
_diffrn_orient_matrix_UB_23      -0.0448
_diffrn_orient_matrix_UB_31      0.0664
_diffrn_orient_matrix_UB_32      -0.0495
_diffrn_orient_matrix_UB_33      0.0200
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710747
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3079
_reflns_number_total             3206
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0520P)²+0.2120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1070
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C4(H4A,H4B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C18(H18), C10(H10), C14(H14), C16(H16), C8(H8), C15(H15), C11(H11),
 C17(H17), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.25299(12) 0.62084(10) 0.88672(7) 0.0300(2) Uani 1 d . . .
O2 O 0.57422(12) 0.71912(8) 0.94662(7) 0.02560(19) Uani 1 d . . .
N1 N 0.54691(13) 0.48026(10) 0.87016(7) 0.0214(2) Uani 1 d . . .
C5 C 0.68365(16) 0.33639(11) 0.70340(9) 0.0202(2) Uani 1 d . . .
C1 C 0.44015(16) 0.60602(12) 0.89948(9) 0.0222(2) Uani 1 d . . .
C7 C 0.79575(16) 0.20828(11) 0.73883(9) 0.0219(2) Uani 1 d . . .
C6 C 0.47875(16) 0.37442(11) 0.76402(9) 0.0221(2) Uani 1 d . . .
H6A H 0.3788 0.4166 0.7173 0.027 Uiso 1 calc . . R
H6B H 0.4147 0.2886 0.7803 0.027 Uiso 1 calc . . R
C13 C 0.63691(16) 0.30306(11) 0.57461(9) 0.0216(2) Uani 1 d . . .
C4 C 0.82090(16) 0.47625(11) 0.75182(9) 0.0223(2) Uani 1 d . . .
H4A H 0.9686 0.4579 0.7437 0.027 Uiso 1 calc . . R
H4B H 0.7801 0.5535 0.7145 0.027 Uiso 1 calc . . R
C12 C 0.74344(19) 0.15386(12) 0.83129(9) 0.0271(2) Uani 1 d . . .
H12 H 0.6310 0.1918 0.8719 0.033 Uiso 1 calc . . R
C18 C 0.75459(19) 0.36338(13) 0.50369(10) 0.0303(3) Uani 1 d . . .
H18 H 0.8650 0.4282 0.5351 0.036 Uiso 1 calc . . R
C10 C 1.0253(2) -0.01438(13) 0.80494(12) 0.0349(3) Uani 1 d . . .
H10 H 1.1014 -0.0880 0.8269 0.042 Uiso 1 calc . . R
C3 C 0.77346(16) 0.51294(11) 0.87643(9) 0.0223(2) Uani 1 d . . .
H3 H 0.8516 0.4508 0.9187 0.027 Uiso 1 calc . . R
C14 C 0.47330(18) 0.20618(13) 0.52460(10) 0.0276(2) Uani 1 d . . .
H14 H 0.3947 0.1628 0.5704 0.033 Uiso 1 calc . . R
C16 C 0.5440(2) 0.23428(13) 0.33817(10) 0.0316(3) Uani 1 d . . .
H16 H 0.5124 0.2123 0.2598 0.038 Uiso 1 calc . . R
C8 C 0.96539(18) 0.14877(13) 0.68004(11) 0.0302(3) Uani 1 d . . .
H8 H 1.0029 0.1834 0.6178 0.036 Uiso 1 calc . . R
C2 C 0.78823(17) 0.67129(12) 0.94304(11) 0.0296(3) Uani 1 d . . .
H2A H 0.8523 0.6785 1.0194 0.036 Uiso 1 calc . . R
H2B H 0.8711 0.7297 0.9049 0.036 Uiso 1 calc . . R
C15 C 0.42523(19) 0.17310(13) 0.40776(10) 0.0319(3) Uani 1 d . . .
H15 H 0.3133 0.1098 0.3761 0.038 Uiso 1 calc . . R
C11 C 0.8575(2) 0.04318(13) 0.86377(10) 0.0330(3) Uani 1 d . . .
H11 H 0.8201 0.0078 0.9257 0.040 Uiso 1 calc . . R
C17 C 0.7092(2) 0.32800(14) 0.38616(11) 0.0341(3) Uani 1 d . . .
H17 H 0.7911 0.3679 0.3397 0.041 Uiso 1 calc . . R
C9 C 1.0790(2) 0.03903(14) 0.71263(13) 0.0364(3) Uani 1 d . . .
H9 H 1.1919 0.0010 0.6724 0.044 Uiso 1 calc . . R

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0211(4) 0.0387(5) 0.0287(4) 0.0043(3) 0.0024(3) 0.0054(3)
O2 0.0240(4) 0.0231(4) 0.0284(4) 0.0027(3) 0.0021(3) 0.0027(3)
N1 0.0181(4) 0.0234(4) 0.0220(4) 0.0042(3) -0.0006(3) -0.0007(3)
C5 0.0182(5) 0.0204(5) 0.0223(5) 0.0055(4) 0.0006(4) -0.0008(4)
C1 0.0226(5) 0.0261(5) 0.0181(5) 0.0052(4) 0.0021(4) 0.0016(4)
C7 0.0211(5) 0.0193(5) 0.0246(5) 0.0050(4) -0.0020(4) -0.0016(4)
C6 0.0186(5) 0.0234(5) 0.0230(5) 0.0029(4) 0.0000(4) -0.0019(4)
C13 0.0212(5) 0.0211(5) 0.0231(5) 0.0061(4) 0.0018(4) 0.0032(4)
C4 0.0187(5) 0.0208(5) 0.0276(5) 0.0060(4) 0.0011(4) -0.0010(4)
C12 0.0348(6) 0.0240(5) 0.0222(5) 0.0042(4) 0.0026(4) 0.0027(4)
C18 0.0318(6) 0.0315(6) 0.0290(6) 0.0098(5) 0.0027(5) -0.0050(5)
C10 0.0349(6) 0.0262(6) 0.0447(7) 0.0137(5) -0.0070(5) 0.0035(5)
C3 0.0178(5) 0.0213(5) 0.0266(5) 0.0040(4) -0.0023(4) -0.0002(4)
C14 0.0270(5) 0.0294(6) 0.0263(5) 0.0058(4) 0.0028(4) -0.0031(4)
C16 0.0405(7) 0.0323(6) 0.0222(5) 0.0071(4) -0.0002(5) 0.0099(5)
C8 0.0244(5) 0.0301(6) 0.0407(7) 0.0160(5) 0.0075(5) 0.0029(4)
C2 0.0216(5) 0.0245(5) 0.0385(6) -0.0007(5) -0.0023(4) 0.0007(4)
C15 0.0319(6) 0.0326(6) 0.0280(6) 0.0018(5) -0.0032(5) -0.0014(5)
C11 0.0477(7) 0.0264(6) 0.0256(6) 0.0086(4) -0.0015(5) 0.0016(5)
C17 0.0428(7) 0.0350(6) 0.0287(6) 0.0144(5) 0.0084(5) 0.0017(5)
C9 0.0253(6) 0.0325(6) 0.0558(8) 0.0172(6) 0.0080(5) 0.0064(5)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2094(14) . ?
O2 C1 1.3561(14) . ?
O2 C2 1.4468(14) . ?
N1 C1 1.3675(14) . ?
N1 C6 1.4730(14) . ?
N1 C3 1.4711(13) . ?
C5 C7 1.5406(14) . ?
C5 C6 1.5538(15) . ?
C5 C13 1.5235(15) . ?
C5 C4 1.5540(15) . ?
C7 C12 1.3906(16) . ?
C7 C8 1.3943(16) . ?
C13 C18 1.3892(16) . ?
C13 C14 1.3921(16) . ?
C4 C3 1.5210(15) . ?
C12 C11 1.3935(16) . ?
C18 C17 1.3921(17) . ?
C10 C11 1.3796(19) . ?
C10 C9 1.3866(19) . ?
C3 C2 1.5311(15) . ?
C14 C15 1.3865(16) . ?
C16 C15 1.3856(18) . ?
C16 C17 1.3779(19) . ?
C8 C9 1.3855(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C2 109.89(8) . . ?
C1 N1 C6 119.08(9) . . ?
C1 N1 C3 110.05(9) . . ?
C3 N1 C6 111.03(9) . . ?
C7 C5 C6 112.46(9) . . ?
C7 C5 C4 108.19(8) . . ?
C6 C5 C4 101.61(8) . . ?
C13 C5 C7 110.02(9) . . ?
C13 C5 C6 110.25(8) . . ?
C13 C5 C4 114.11(9) . . ?
O1 C1 O2 122.17(10) . . ?
O1 C1 N1 127.17(11) . . ?
O2 C1 N1 110.66(9) . . ?
C12 C7 C5 123.04(10) . . ?
C12 C7 C8 117.95(10) . . ?
C8 C7 C5 118.91(10) . . ?
N1 C6 C5 104.46(8) . . ?
C18 C13 C5 122.55(10) . . ?
C18 C13 C14 118.03(10) . . ?
C14 C13 C5 119.41(10) . . ?
C3 C4 C5 102.19(9) . . ?
C7 C12 C11 120.80(11) . . ?
C13 C18 C17 120.78(12) . . ?
C11 C10 C9 119.13(11) . . ?
N1 C3 C4 102.63(9) . . ?
N1 C3 C2 102.05(9) . . ?
C4 C3 C2 119.47(10) . . ?
C15 C14 C13 121.26(11) . . ?
C17 C16 C15 119.43(11) . . ?
C9 C8 C7 121.19(11) . . ?
O2 C2 C3 105.40(9) . . ?
C16 C15 C14 120.00(11) . . ?
C10 C11 C12 120.60(12) . . ?
C16 C17 C18 120.47(11) . . ?
C8 C9 C10 120.33(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
